1-dodecylaminomethyl-2-amino-cyclopentane

ABSTRACT

This invention relates to the novel microbiocidally active compound 1-dodecylaminomethyl-2-amino-cyclopentane, and to a process for the preparation thereof. The invention also relates to a microbiocidally active composition including the microbiocidally active compound and a carrier.

United States Patent Holtschmidt et' al.

1-DODECYLAMINOMETHYL-Z-AMINO- CYCLOPENTANE Inventors: Ulrich Holtschmidt, Essen; Giinter Schwarzmann, Essen-Uberruhr, both of Germany Assignee: Th. Goldschmidt AG, Germany Filed: July 30, 1973 Appl. No.: 383,679

Foreign Application Priority Data Sept. 13, 1972 Germany 2244778 US. Cl 260/563 R; 424/325; 260/585 A Int. Cl. C07C 87/38 Field of Search 260/585 A, 563; 424/325 July 22, 1975 [56] References Cited UNITED STATES PATENTS 3,227,761 l/l966 DeBrunner et al. 260/585 A Primary ExaminerLewis Gotts Assistant ExaminerD. R. Phillips Attorney, Agent, or Firm-James E. Bryan [57] ABSTRACT 1 Claim, No Drawings l -DODECYLAMlNOMETHYL-Z-AMINO- CYCLOPENTANE The present invention relates to the new compound, with microbiocidal properties, l-dodecylaminomethyl- 2-amino-cyclopentane, as well as to a process for producing this compound, and to the use thereof as an active microbiocidal substance.

Microbiocidal action in the sense of the present invention means the destruction of Gram-positive as well as Gram-negative bacteria, fungi, and yeasts. This constitutes the primary activity thereof, but the novel compound also develops a certain efficacy with respect to viruses and algae.

In the use of microbiocidally-active compounds it is desirable that one have available a broad spectrum of diversified chemical compounds in order to prevent that resistant strains be formed in the bacteria and the like to be destroyed, and/or that strains which already have become resistant can be again combated successfully. The manufacture of a new class of microbiocidally-active compounds thus enriches the state of the art.

The present invention relates to a novel active substance which, as compared to the known active materials, has the specific advantage that it is effective especially against a number of bacteria, fungi, and yeasts which are relatively difficult to combat and which are very frequently responsible for the so-called hospitalism. This term is understood as the spreading of pathogenic germs, particularly in hospitals, which are characterized by a high resistance against microbiocidal compounds. Examples of such germs are S. aureus, P. aeruginosa, and K. pneumoniae.

The novel microbiocidally-active compound is ldodecylaminomethyl-2-amino-cyclopentane which can be represented by the following formula c H 12 25 on N 2 The basic diamine is without effect. The optimal effect appears with the substitution of a hydrogen, linked to the nitrogen of the aminomethyl group, by one dode cyl group. If a second dodecyl group is introduced, the

. solubility of the compound is impaired to such a degree This compound may be prepared by reacting laminomethyl-2-aminocyclopentane with approximately halfmolar amounts of dodecyl halide, preferably dodecyl chloride, heating after the termination of the exothermic reaction for at least 1 hour to temperatures of to 150C, freeing the reaction mixture from the residue, and separating the desired compound from the reaction mixture, preferably by fractional distillation.

aqueous or aqueous-alcoholic solutions, it is therefore necessary to use a solution aid during the production of the preparation containing this compound. Examples of suitable solution aids are, for instance, the addition products of ethylene oxide to higher alcohols, such as for example tridecyl alcohol, or cation-active compounds, such as for example dodecyl dimethylbenzylammonium-choride. These solubilizing agents are employed in approximately equal amounts based upon active substance.

Theinventive compound may be mixed in solution in the customary manner, i.e., the dissolved and/or solubilized compound may be mixed together with other microbiocidal compounds and with other additions, such as odorous substances or dyestuffs. The compound also may be dissolved in fluorinated chlorinated hydrocarbons and used in aerosol form. By virtue of the addition of the solubilizing agents when using an aqueous solution, the purifying power of the solutions is enhanced at the same time, and specifically when nonionogenic tensides are used as solubilizing agents.

In the following example, the novel process will first be explained. Thereafter, the efficacy of the inventively prepared compound will be shown in table form. The testing relative to microbiocidal action was made according to the Richtlinien der Deutschen Gesellschaft fuer Hygiene und Mikrobiologie e.V., (Guidelines of the German Society for Hygiene and Microbiology) Gustav Fischer Verlag, Stuttgart, 1959. In the tables, means germ growth, means no germ growth.

EXAMPLE Preparation of l-dodecylaminomethyl-2-amino-cyclopentane Placed in a four-liter four-necked flask, equipped with a KPG stirrer, dropping funnel, thermometer, and reflux condenser, are 8 moles of Z-amino-methyl-Z- amino-cyclopentane and 6.4 moles of NaOH. Added slowly to this mixture are 4 moles of dodecylbromide,

' and heating is thereafter effected at C for 5 hours.

calculated found C 76.5% by weight C 76.7% by weight H 13.6% by weight "H 13.6% by weight N 9.9% by weight N 9.5% by weight In a further fraction, 368 grams of 1- dodecylaminomethyl-2-dodecy1amino-cyclopentane pass over, between 201 and 205C and at 10' Torr.

Elemental analysis for C H N (molecular weight 5 451):

For the testing of the microbiocidal efficacy, the following preparations were made: Preparation 1 parts by weight of l-dodecylaminomethyl-2- amino-cyclopentane, 10 parts by weight of an addition product of 12 moles of ethylene oxide to 1 mole of isotridecyl alcohol, 10 parts by weight of acetic acid and 70 parts by weight of water are homogenized, while stirring, and heating to approximately 40C. Thus obtained is a yellow-colored, clear solution which easily can be diluted with water. Preparation 2 10 parts by weight of l-dodecylaminomethyl-2- amino-cyclopentane, 10 parts by weight of a solution which contains 80% by weight of and 20% by weight of ethanol, as well as 10 parts by weight of acetic acid, and 70 parts by weight of water are homogenized, while stirring, at approximately I 40C. A yellow clear solution is obtained which can be mixed with water in anyproportion. Preparation 1 The pH value of the aqueous solution containing 0.1% of active substance was adjusted with acetic acid to 7.3.

T. menta- -Continued Concentration in Test Strain P. vulgaris P. aeruginosa g'rophytes Preparation 2 The pH value of the aqueous solution containing 0.1% of active substance was adjusted with acetic acid to 7.6.

Action time in minutes 10 20 Concentration Test Strain S. aureus E. coli P. vulgaris P. aeruginosa M. gypseum K. pneumoniae Test Strain Concentration Action time in minutes Test Strain Concentration Action time in minutes in l 20 30 i 20 30 aul'eus S. aureus 0.1

0.05 0.05 0.01 Q0] 0005 v 0.005 O-OOI E. coli 1.0

0.5 0.05 P. aeruginosa 2.0 0.01 1.0 0005 0.5

-Continued Test Strain Concentration Action time in minutes in l 2 5 2O 30 C. albicans 5.0 2.5 1.0 P. expansum 5.0 2.5 LO

A comparison of the tables shows the superiority of l. l-dodecylaminomethyl-2-amino-cyclopentane. 

1. 1-DODECYLAMINOMETHYL-2-AMINO-CYCLOPENTANE. 